(S)-1-(3-bromophenyl)ethyl alcohol-O-(tert-butyldimethylsilyl) ether

Base Information

• Chemical Name: (S)-1-(3-bromophenyl)ethyl alcohol-O-(tert-butyldimethylsilyl) ether
• CAS No.: 871841-05-3
• Molecular Formula: C₁₄H₂₃BrOSi
• Molecular Weight: 315.326
• Mol file: 871841-05-3.mol

Synonyms:(S)-1-(3-bromophenyl)ethyl alcohol-O-(tert-butyldimethylsilyl) ether

Chemical Property of (S)-1-(3-bromophenyl)ethyl alcohol-O-(tert-butyldimethylsilyl) ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-(3-bromophenyl)ethyl alcohol-O-(tert-butyldimethylsilyl) ether

There total 1 articles about (S)-1-(3-bromophenyl)ethyl alcohol-O-(tert-butyldimethylsilyl) ether which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (S)-1-(3-bromophenyl)ethan-1-ol (134615-22-8) → (S)-1-(3-bromophenyl)ethyl alcohol-O-(tert-butyldimethylsilyl) ether (871841-05-3)

Guidance literature:

With 15-crown-5; sodium hydride; In dichloromethane; at 20 ℃; for 0.916667h;

DOI:10.1016/j.tet.2005.09.007

Reference yield: 91.0%

(S)-1-(3-bromophenyl)ethyl alcohol-O-(tert-butyldimethylsilyl) ether (871841-05-3) + N,N-diethyl-2,2,2-trifluoroacetamide (360-92-9) → (S)-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2,2,2-trifluoroacetophenone (871841-07-5)

Guidance literature:

(S)-1-(3-bromophenyl)ethyl alcohol-O-(tert-butyldimethylsilyl) ether; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.25h;

N,N-diethyl-2,2,2-trifluoroacetamide; In tetrahydrofuran; hexane; at -78 ℃; for 1.25h;

DOI:10.1016/j.tet.2005.09.007

Reference yield:

(S)-1-(3-bromophenyl)ethyl alcohol-O-(tert-butyldimethylsilyl) ether (871841-05-3) → (S)-1-[3-(3-trifluoromethyl-3H-diazirin-3-yl)phenyl]ethyl alcohol (871841-14-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1.25 h / -78 °C

1.2: 91 percent / tetrahydrofuran; hexane / 1.25 h / -78 °C

2.1: 99 percent / hydroxylamine hydrochloride; pyridine / ethanol / 4 h / 80 °C

3.1: 82 percent / DIEA; DMAP / CH₂Cl₂ / 0.67 h / 0 - 20 °C

4.1: 79 percent / ammonia / diethyl ether / 2 h / -78 °C

5.1: 96 percent / pyridine; PCC / CH₂Cl₂

6.1: 82 percent / TBAF / tetrahydrofuran; H₂O / 2 h / 20 °C

With pyridine; dmap; n-butyllithium; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; ammonia; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water;

DOI:10.1016/j.tet.2005.09.007

upstream raw materials:

tert-butyldimethylsilyl chloride

(S)-1-(3-bromophenyl)ethan-1-ol

Downstream raw materials:

(S)-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2,2,2-trifluoroacetophenone

(S)-1-[3-(3-trifluoromethyl-3H-diazirin-3-yl)phenyl]ethyl alcohol

(R)-1-[3-(3-trifluoromethyl-3H-diazirin-3-yl)phenyl]ethylamine

(S)-1-[3-(3-trifluoromethyl-3H-diazirin-3-yl)phenyl]ethyl alcohol-O-tert-butyldimethylsilyl ether